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Questions for Improving Strategy
Dr. Julia Sloan

Here are five tips for asking good strategy questions. Let me ask you, what are some good strategy questions? Strategy leaders have a responsibility to develop an ability to listen for and to ask good questions about their strategy. This sounds easier than it is, because many times, our own habits and organizational habits create constraints around strategy questions. Have you ever watched a group of executives hone in to problem solving, rather than taking time to get clear about the real strategy question? I’m suggesting we need to open up the strategy issue before closing it with a solution that may or may not address the real problem. Asking good questions triggers critical reflection, which in turn can lead to critical dialogue – two essentials for strategic thinking. We use questions as a means of testing and challenging strategy assumptions. Questions are a critical tool for seeing if our strategy actually holds water.

What kinds of questions do you routinely hear in your strategy sessions? Do you ever get a question that makes you stop in your tracks? Or a question for which you don’t have an answer? And what about that one that just makes you scratch your head? Most questions that I routinely hear in the strategy meetings I attend, allow people to stay on the surface; they’re what I call Surf level questions. They sound like, “How much is this going to cost? What’s your budget? What are our competitors margins? How much time are we looking at? What do the numbers say?” There’s nothing wrong with these Surf level questions, in fact we need them because they provide information and are efficient. They help us get the necessary information to make decisions, and they help us avoid surprises.

By contrast, Dive level questions do just what the word suggests; they dive deeper and they get at the premise of our strategy. In my research and consulting work, I find them to be extremely rare. I find that most of the time Dive level questions are avoided altogether in strategy sessions for a number of reasons. They take time, they make us sweaty and squirm, they don’t have clear-cut answers, they generate even more questions, and they’re just plain messy. That’s exactly what they’re intended to do. Dive level questions uncover and expose fundamental assumptions about the strategy. They challenge and test what a product strategy or a sales or business unit strategy is all about.

Be honest about your emotional attachment to your strategy. It needs to be intense if you’re going to have the conviction to drive a strategy. At the same time, this emotional attachment is exactly what makes it feel like you’re being kicked in the gut when somebody does a deep Dive question. Strategy leaders have a responsibility to create an environment and step up to the plate by modeling and inviting Dive level questions. How?

1. Know the difference between Surf and Dive level questions.

2. Check your ego. Check your strategy history. Check your habit-of-mind.

3. Model Dive level questions during meetings as a way of giving permission.

4. Let people know the purpose of asking Dive level questions; it’s for the sake of the business.

5. Practice rounds of encouraging Dive level questions in meetings.

Strategy is enormously complex and risky. If we avoid Dive level questions, we actually end up creating risk in the long term. What kind of questions do you invite and model within your strategy sessions?

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